Nitrogen → 5-Benzyl-octahydropyrrolo(3,4-c)pyrrole-1,3-dione

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Reaction Steps

To the maleimide (80.4 g, 0.83 mol) in 1.5 L of CH2Cl2 in a 3-neck, 3-L round bottom flask equipped with an addition funnel, internal thermometer, and N2 inlet at 0° C. was added trifluoroacetic acid (TFA) (6.4 mL, 83 mmol). Benzyl(methoxymethyl)trimethylsilylmethylamine (261 g, 1.1 mol) in 500 mL CH2Cl2 was added dropwise via addition funnel over 3 hours with the reaction temperature being maintained below 5° C. After the addition was complete, the mixture was allowed to warm slowly to ambient temperature and then was stirred for 16 h. The mixture was concentrated and the residue was dissolved in 500 mL CH2Cl2 and was washed with 2×50 mL saturated NaHCO3. The layers were separated and the aqueous layer was extracted 2×25 mL CH2Cl2. The combined organics were washed with 25 mL brine, dried over saturated, aqueous Na2SO3, and concentrated under reduced pressure to give the title compound which was carried on to the next step without further purification. MS (DCl/NH3) m/z 231 (M+H)+.

Provenance & Evidence